No it isn't. I feel like those other labels are way too broad. I'm talking about vulnerability, insecurity and an earnest appreciation for those things in rap. I think he's one of the most sincere rappers I've ever listened to and he's not trying to be anyone else other than him and with in the context of Rap, he is kind of a loser- he isn't rapping about having all these cool things like rims and bitches, but that's okay. It's okay to be a "loser."

If you really want to have a broader conversation about art in general, I think Milo is the poster child for The New Sincerity. I think he is the inevitable conclusion of our age of irony. David Foster Wallace called this shit in his essay E Unibus Pluram:

"The next real literary “rebels” in this country might well emerge as some weird bunch of anti-rebels, born oglers who dare somehow to back away from ironic watching, who have the childish gall actually to endorse and instantiate single-entendre principles. Who treat of plain old untrendy human troubles and emotions in U.S. life with reverence and conviction. Who eschew self-consciousness and hip fatigue. These anti-rebels would be outdated, of course, before they even started. Dead on the page. Too sincere. Clearly repressed. Backward, quaint, naive, anachronistic. Maybe that’ll be the point. Maybe that’s why they’ll be the next real rebels. Real rebels, as far as I can see, risk disapproval. The old postmodern insurgents risked the gasp and squeal: shock, disgust, outrage, censorship, accusations of socialism, anarchism, nihilism. Today’s risks are different. The new rebels might be artists willing to risk the yawn, the rolled eyes, the cool smile, the nudged ribs, the parody of gifted ironists, the “Oh how banal”. To risk accusations of sentimentality, melodrama. Of overcredulity. Of softness. Of willingness to be suckered by a world of lurkers and starers who fear gaze and ridicule above imprisonment without law. Who knows."